From the album 14:14, released September 1999.
Words: J. Thornett

Bobby was a gambling man from dawn to evening light
Never one to show his hand he lost it all each night
But when time came to go home, Bobby would turn and say
How about one final go, I'm sure my luck's gonna change

(Chorus)
So just one more go and I know I'll win
Tell you what, double or quits
Just one more go and I know I'll win
I'm gonna beat this thing

He bet everything he owned and then even more besides
Gambled away his home and bid farewell to his wife
But then as his girl was leaving he chased her down the drive
Said I know what you must be thinking but I will change this time

(Chorus)

So in the early hours of morning at a card game up in town
Bobby swore he wasn't leaving till he'd beaten them to the ground
He bluffed and he upped the stakes until the morning sun shone
Then he lost it all on a pair of eights and everything was gone

(Chorus)

Now bobby's up there somewhere smiling down at us
He knows the world ain't fair unless your blessed with luck
Now as bobby sits there on his cloud an angel comes walking by
Bobby turns to look at her with a pleading in his eye

(Chorus)